Ethyl Acetate → HCID 70674227, compound

HRID 1747719Notes

Reaction equation

HRID 1747719 reaction equation
[F:1][C:2]1[CH:19]=[CH:18][CH:17]=[CH:16][C:3]=1[CH2:4][C:5]1[N:9]2[N:10]=[CH:11][CH:12]=[CH:13][C:8]2=[C:7]([C:14]#[N:15])[N:6]=1.[C:20]([NH:22][C:23]([NH2:25])=[NH:24])#[N:21].[OH-].[Na+].[C:28]([O:31]CC)(=[O:30])C>CS(C)=O>[CH:28]([OH:31])=[O:30].[F:1][C:2]1[CH:19]=[CH:18][CH:17]=[CH:16][C:3]=1[CH2:4][C:5]1[N:9]2[N:10]=[CH:11][CH:12]=[CH:13][C:8]2=[C:7]([C:14]2[N:24]=[C:23]([NH2:25])[N:22]=[C:20]([NH2:21])[N:15]=2)[N:6]=1

Participants

6

Reactant 4

HCID 8857Ethyl AcetateHCID 14798Sodium HydroxideHCID 70983445HCID 70983445, compoundHCID 178418324HCID 178418324, compound

Product 1

HCID 70674227HCID 70674227, compound

Reagents, catalysts & solvents 1

HCID 679Dimethyl SulfoxideSolvent

Procedure

100 mg (0.4 mmol) of 7-(2-fluorobenzyl)imidazo[1,5-b]pyridazine-5-carbonitrile (Example 6A) and 60 mg (0.71 mmol) of 1-cyanoguanidine in 1.3 ml of DMSO were stirred with 4.8 mg (0.12 mmol) of sodium hydroxide at 150° C. in a microwave reactor for 40 minutes. At 20° C., the reaction mixture was then diluted with ethyl acetate (50 ml) and washed twice with in each case 20 ml of water. Purification by HPLC (acetonitrile:water (+0.1% formic acid) gradient) and concentration of the product-containing fractions gave 37.2 mg (25% of theory) of the target compound.

Workup

  1. washwashed twice with in each case 20 ml of water
  2. customPurification by HPLC (acetonitrile:water (+0.1% formic acid) gradient) and concentration of the product-containing fractions
  3. customgave 37.2 mg (25% of theory) of the target compound

Sources & evidence

ORD record
ord-d5f8c001757e436b9bf2031c05890baf
Source dataset
uspto-grants-2015_10
Patent number
US09150580B2

Reaction notes

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